37616-35-6Relevant articles and documents
Alkyl- and Arylthiodediazoniations of Dry Arenediazonium o-Benzenedisulfonimides. Efficient and Safe Modifications of the Stadler and Ziegler Reactions to Prepare Alkyl Aryl and Diaryl Sulfides
Barbero, Margherita,Degani, Iacopo,Diulgheroff, Nicola,Dughera, Stefano,Fochi, Rita,Migliaccio, Mara
, p. 5600 - 5608 (2007/10/03)
The reaction between dry arenediazonium o-benzenedisulfonimides 1 and sodium thiolates in anhydrous methanol represents an efficient and safe procedure, of general validity, for the preparation of unfunctionalized or variously functionalized alkyl aryl and diaryl sulfides. As a rule, the reaction temperature was maintained at 0-5°C for the alkylthiodediazoniations and at room temperature (20-25°C) for the arylthiodediazoniations. The sulfide yields are generally high; of the 63 considered examples, 43 gave yields greater than 80% and 13 were between 70% and 80%. Lower yields were obtained only when sterically hindered diazonium salts or thiols were used. A good amount of the o-benzenedisulfonimide (8) was always recovered from the reactions and could be reused to prepare salts 1. The copious experimental data collected in homogeneous conditions have offered several starting points for the study of the mechanism of these reactions.
Chemoselective alkylation of thiols: A detailed investigation of reactions of thiols with halides
Khurana,Sahoo
, p. 1691 - 1702 (2007/10/02)
Arylthiols, aralkylthiols and alkane thiols can be readily alkylated by alkyl/aralkyl halides in presence of K2CO3/DMF to yield unsymmetrical sulphides in nearly quantitative yields. 2-Mercaptoethanol gave the thioether chemoselectively.
Betylates. 4. The synthesis and preparative nucleophilic substitution reactions of alkyl S-betylates
King, James Frederick,Skonieczny, Stanislaw,Poole, Gary Allan
, p. 235 - 243 (2007/10/02)
Alkyl S-betylates (S,S-dialkyl-S-3propylsulfonium salts), the first examples of S-betylates (sulfonioalkanesulfonic esters), have been synthesized by two routes, and their suitability as intermediates in the transformation of alcohols by nucleophilic substitution reactions examined.They have been found to react readily in stoichiometric phase transfer processes, including substrate-reagent ion-pair reactions, like their previously studied nitrogen analogues, with the following particular features: (a) they may be used with basic nucleophiles (unlike betylates), (b) they are more simply made from commercially available starting materials than betylates, and (c) they can be made by a route that avoids a final alkylation step.
